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26577-85-5

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Basic Information
CAS No.: 26577-85-5
Name: PETASIN
Article Data: 2
Molecular Structure:
Molecular Structure of 26577-85-5 (PETASIN)
Formula: C20H28 O3
Molecular Weight: 316.441
Synonyms: 2-Butenoicacid, 2-methyl-,1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenylester, [1R-[1a,2b(Z),7b,8aa]]-; Eremophila-9,11-dien-8-one, 3a-hydroxy-, 2-methylcrotonate, (Z)- (8CI); Petasin(6CI,7CI); Crotonic acid, 2-methyl-, ester with 3a-hydroxy-eremophila-9,11-dien-8-one, (Z)- (8CI);(+)-Petasin; Petaforce
Density: 1.04g/cm3
Melting Point: 66-70℃
Boiling Point: 421.1°Cat760mmHg
Flash Point: 181.6°C
PSA: 43.37000
LogP: 4.39210
Related products
Synthetic route
164414-38-4

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester

A

469-26-1

Isopetasin

B

26577-85-5

Petasin

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1h;A 17%
B 69%
164414-38-4

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester

26577-85-5

Petasin

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1h;69%
565-63-9

Angelic acid

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / toluene / 2 h / Ambient temperature
2: Et3N / toluene / 24 h / 80 °C
3: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme
137601-32-2

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / toluene / 24 h / 80 °C
2: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme
122052-66-8

(4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) HMDS, 3.) ZnCl2
2: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature
3: Et3N / toluene / 24 h / 80 °C
4: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme
164577-44-0

(3S,4aR,5R,6R)-(+)-6-hydroxy-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / toluene / 24 h / 80 °C
2: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme
164414-36-2

(1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: toluene / 5 h / 80 °C
2: ethanol / 15 h / Heating
3: 1.) HMDS, 3.) ZnCl2
4: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature
5: Et3N / toluene / 24 h / 80 °C
6: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme
164414-37-3

(3S,4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature
2: Et3N / toluene / 24 h / 80 °C
3: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme

5-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-6-oxo-cyclohexyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanoic acid phenylamide

26577-85-5

Petasin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ethanol / 15 h / Heating
2: 1.) HMDS, 3.) ZnCl2
3: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature
4: Et3N / toluene / 24 h / 80 °C
5: 69 percent / (CF3SO2)O, i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
View Scheme
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